title: Stereoselective preparation of lipidated carboxymethyl-proline/pipecolic acid derivatives via coupling of engineered crotonases with an alkylmalonyl-CoA synthetase.
abstract: The trisubstituted enolate- and C-C bond-forming capacities of engineered carboxymethylproline synthases CMPSs are coupled with the malonyl-CoA synthetase MatB to enable stereoselective preparation of 5- and 6-membered N-heterocycles functionalised with alkyl-substituted carboxymethyl side chains, starting from achiral alkyl-substituted malonic acids and L-amino acid semialdehydes. The results illustrate the biocatalytic utility of crotonases in tandem enzyme-catalysed reactions for stereoselective synthesis.
authors.affiliation: Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK. christopher.schofield@chem.ox.ac.uk.
authors.forename: Refaat B
authors.initials: RB
authors.lastname: Hamed
authors.forename: Luc
authors.initials: L
authors.lastname: Henry
authors.forename: J Ruben
authors.initials: JR
authors.lastname: Gomez-Castellanos
authors.forename: Amina
authors.initials: A
authors.lastname: Asghar
authors.forename: Jürgen
authors.initials: J
authors.lastname: Brem
authors.forename: Timothy D W
authors.initials: TD
authors.lastname: Claridge
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Schofield
mesh_terms: D001426:Bacterial Proteins / Q000737:chemistry / Q000378:metabolism*; D055162:Biocatalysis; D003066:Coenzyme A Ligases / Q000737:chemistry / Q000378:metabolism*; D004746:Enoyl-CoA Hydratase / Q000737:chemistry / Q000378:metabolism*; D008055:Lipids / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010875:Pipecolic Acids / Q000737:chemistry / Q000378:metabolism*; D011392:Proline / Q000096:biosynthesis* / Q000737:chemistry; D015202:Protein Engineering; D013237:Stereoisomerism
chemical_list: D001426:Bacterial Proteins; D008055:Lipids; D010875:Pipecolic Acids; D011392:Proline; D004746:Enoyl-CoA Hydratase; D003066:Coenzyme A Ligases; C021533:malonyl-CoA synthetase; C031345:pipecolic acid